Jason,
I was an ASP and
ASP.NET developer for several years too. I switched
to Ruby nearly 2 years ago and have been amazingly more happy and
productive since. The language and tools are much more expressive and
powerful. AJAX and Javascript through RJS is stupid simple. Check
out the
http://www.Rubyology.com podcast to help with your transition!
Cheers,
Chris Matthieu